Sulfated zirconia-catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) under solventless conditions: Competitive multicomponent Biginelli vs. Hantzsch reactions

Molecules

Volumn 11, Issue 10, 2006, Pages 731-738

  Angeles Beltrán, Deyanira ^a   Lomas Romero, Leticia ^a   Lara Corona, Victor H ^a   González Zamora, Eduardo ^a   Negrón Silva, Guillermo ^a  

^a UNIVERSIDAD AUTÓNOMA METROPOLITANA   (Mexico)

Author keywords

1,4 Dihydropyridines; Biginelli reaction; Dihydropyrimidinones; Hantzsch reaction; Multicomponent reactions; Solventless reactions

Indexed keywords

PYRIMIDINONE DERIVATIVE; SOLVENT; SULFATE; ZIRCONIUM; ZIRCONIUM OXIDE;

ARTICLE; CATALYSIS; CHEMISTRY; COMPARATIVE STUDY; SYNTHESIS;

CATALYSIS; PYRIMIDINONES; SOLVENTS; SULFATES; ZIRCONIUM;

EID: 33750530399     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/11100731     Document Type: Article

References (39)

1. a) Lu, J.; Bai, Y.; Wang, A.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 18, 9075-9078 ;
2. b) Ma, Yun.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000, 62, 3864-3868 ;
3. c) Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270-6272.
4. Varma, R. S. Tetrahedron 2002, 58, 1235-1255.
5. Corma, A.; García, H. Chem. Rev, 2003, 103, 4307-4366.
6. Sen, S. E.; Smith, S. M.; Sullivan, K. A. Tetrahedron 1999, 55, 12657-12698.
7. Song, X.; Sayari, A. Cat. Rev. Sci. Eng. 1996, 38, 329-412.
8. Benjaram, M. R.; Pavani, M.S. Tetrahedron Lett. 2003, 44, 4447-4449.
9. Negrón, G.; Angeles, D.; Lomas, L.; Martínez, A.; Ramírez, M.; Martínez, R. Heterocycles 2004, 63, 367-371.
10. Deutsch, J.; Trunschke, A.; Muller, D.; Quaschning, V.; Kemnitz, E.; Lieske, H. Catalysis Lett. 2003, 88, 9-15.
11. Toshima, K.; Nagai, H.; Kasumi, K.; Kawahara, K.; Matsumura, S. Tetrahedron 2004, 60, 5331-5339.
12. Wolfson, A.; Shokin, O.; Tavor, D. J. Mol. Catal. A. 2005, 226, 69-76.
13. Biró, K.; Figueras, F.; Békássy, S. Appl. Catal. A: Gen. 2002, 229, 235-243.
14. Negrón, G.; Palacios, L.; Angeles, D.; Lomas, L.; Gaviño, R. J. Braz. Chem. Soc. 2005. 16, 490-494.
15. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025-1074.
16. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360-416.
17. a) Kappe, O. Tetrahedron 1993, 49, 32, 6937-6963;
18. b) Kappe, O. J. Org. Chem. 1997, 62, 3109-3118.
19. Lin, H.; Ding, J.; Chen, X.; Zhang, Z. Molecules 2000, 5, 1240-1243.
20. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Fard, M. A. B. Heterocycles 2003, 60, 2435-2440.
21. Juaristi, E.; Muñoz-Muñiz, O. ARKIVOC 2003, XI, 16-26.
22. Gohain, M.; Prajapati D ; Sandhu J. S. Synlett., 2004, 2, 235-238.
23. Cepanec, I.; Litvic, M.; Bartolinčić, A.; Lovrić, M. Tetrahedron, 2005, 61, 4275-4280.
24. a) Reddy, B. M.; Sreekanth, P. M.; Reddy, V. R. J. Mol. Catal. A: Chem. 2005, 225, 71-78;
25. b) Reddy, B. M.; Sreekanth, P. M.; Lankshmanan, P. J. Mol. Catal. A: Chem. 2005, 237, 93-100;
26. c) Singh V.; Sapehiyia V.; Srivastava V.; Kaur S. Catal. Commun. 2006, 7, 571-578.
27. Stout, D. M. Chem. Rev. 1982, 82, 223-243.
28. Zolfigol, M. A.; Safaiee, M. Synlett 2004, 5, 827-828.
29. a) Janis, R. A.; Silver, P. J.; Triggle, D. J, Adv. Drug Res. 1987, 16, 309-591;
30. b) Bossert, F.; Meyer, H.; Wehinger, E. Angew. Chem. Int. Ed. Eng. 1981, 20, 762-769.
31. Osnaya, R.; Arroyo, G. A.; Parada, L.; Delgado, F.; Trujillo, J.; Salmón, M.; Miranda, R., ARKIVOC 2003, XI, 112-117.
32. Legay, J.C.; Vanden, E. J. J.; Bazureau, J. P. Tetrahedron 2005, 61, 12386-12397.
33. Sridhar, R.; Perumal, P. T. Tetrahedron 2005, 61, 2465-2470.
34. Salehi, H.; Guo, P. X. Synth. Commun. 2004, 34, 4349-4357.
35. Yutaka, W.; Kazuhiro, S.; Tomonori, H.; Shoichiro, O. Synthesis 1983, 9, 759-761.
36. Liselotte, O.; Westman, J. Synlett 2001, 8, 1296-1298.
37. Khodabakhsh, N.; Mohammah, Z.; Mehdi, S.; Iraj, M. Heterocycles 2005, 65, 657-660.
38. Zhidovinova, M. S.; Fedorova, O.V.; Rusinov, G.L.; Ivchinnikova, I. G. Rus. Chem. Bull. 2003, 52, 2527-2528.
39. Stichert, W.; Schüth, F.; Kuba, S.; Knüozinger, H. J. Catal. 2001, 198, 277-285.